trimethylsilyl 2-(diethoxyphosphoryl)acetate

• ChemBase ID: 74951
• Molecular Formular: C9H21O5PSi
• Molecular Mass: 268.319301
• Monoisotopic Mass: 268.08958693
• SMILES: P(=O)(OCC)(OCC)CC(=O)O[Si](C)(C)C
• Canonical SMILES: CCOP(=O)(CC(=O)O[Si](C)(C)C)OCC
• InChI: InChI=1S/C9H21O5PSi/c1-6-12-15(11,13-7-2)8-9(10)14-16(3,4)5/h6-8H2,1-5H3
• InChIKey: VHIDZGBMGSRVHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethylsilyl 2-(diethoxyphosphoryl)acetate
• IUPAC Traditional name: trimethylsilyl 2-(diethoxyphosphoryl)acetate
• Synonyms: Diethyl(2-trimethylsiloxycarbonyl)phosphonate; Phosphonoacetic acid P,P-diethyl trimethylsilyl ester; Diethyl (trimethylsilyloxycarbonylmethyl)phosphonate; Trimethylsilyl P,P-diethylphosphonoacetate; (三甲基硅氧羰基甲基)膦酸二乙酯; 三甲基硅烷二乙基磷酰乙酸酯

Database IDs

• CAS Number: 66130-90-3
• EC Number: 266-171-0
• MDL Number: MFCD00009080
• Beilstein Number: 2371028
• PubChem SID: 24856362; 24887463; 162039869
• PubChem CID: 171755

CALCULATED PROPERTIES

• Acid pKa: 16.923773
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6924
• LogD (pH = 7.4): 1.6924
• Log P: 1.6924
• Molar Refractivity: 58.5085 cm^3
• Polarizability: 25.805046 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 93 °C/0.05 mmHg
• Flash Point: 15 °C; 59 °F
• Density: 1.059 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.430(lit.)

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H315-H319-H335
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Linear Formula: (C2H5O)2P(O)CH2CO2Si(CH3)3

DETAILS

Sigma Aldrich - 270210

Packaging
5, 25 mL in glass bottle
Application
Used in the synthesis of cytovaricin.1

Sigma Aldrich - 79520

Other Notes
A Horner-Wittig reagent for the preparation of α,β-unsaturated acids1,2